Crystal structure of ethyl 2-[2-((1E)-{(1E)-2-[2-(2-eth­oxy-2-oxoeth­oxy)benzyl­idene]hydrazin-1-yl­idene}meth­yl)phen­oxy]acetate

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Ahmed, E.A.; Omran, O.A.

doi:10.1107/S2056989014025584

organic compounds

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https://doi.org/10.1107/S2056989014025584

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Crystal structure of ethyl 2-[2-((1E)-{(1E)-2-[2-(2-ethoxy-2-oxoethoxy)benzylidene]hydrazin-1-ylidene}methyl)phenoxy]acetate

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Eman A. Ahmed ^e ^* and Omran A. Omran ^e

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt
^*Correspondence e-mail: abdala_15@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 16 November 2014; accepted 23 November 2014; online 1 January 2015)

The complete molecule of the title compound, C₂₂H₂₄N₂O₆, is generated by crystallographic inversion symmetry and is approximately planar (r.m.s. deviation of the non-H atoms = 0.134 Å). The packing consists of inter-digitated sheets inclined at 25.9 (4)° to one another and linked by short C—H⋯O hydrogen bonds.

Keywords: crystal structure; azomethenes; bis-phenoxy carboxylate.

CCDC reference: 1035485

1. Related literature

For background to the properties and applications of imines see: Sun et al. (2001 ); Boghaei & Mohebi (2002 ); Liu et al. (2006 ); Britovsek et al. (2001 ); Budakoti et al. (2006 ).

2. Experimental

2.1. Crystal data

C₂₂H₂₄N₂O₆
M_r = 412.43
Monoclinic, C 2/c
a = 18.2073 (5) Å
b = 11.7758 (3) Å
c = 9.9950 (3) Å
β = 93.226 (1)°
V = 2139.59 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 150 K
0.16 × 0.15 × 0.07 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.88, T_max = 0.94
12339 measured reflections
2124 independent reflections
1801 reflections with I > 2σ(I)
R_int = 0.032

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.094
S = 1.06
2124 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.34	3.2802 (14)	168
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Bruker, 2014).

Supporting information

CCDC reference: 1035485

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989014025584/hb7321sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014025584/hb7321Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014025584/hb7321Isup3.cml

checkCIF report

Comment top

Imines are used as catalysts, in medicine as antibiotics and anti-inflammatory agents and in industry as anticorrosion agents (Sun et al., 2001; Boghaei & Mohebi, 2002; Liu et al., 2006; Britovsek et al., 2001; Budakoti et al., 2006). Based on these finding we report here the synthesis and crystal structure of the title compound.

The title molecule has crystallographically imposed centrosymmetry with an "extended" conformation in which the central portion is almost planar. Intermolecular C6—H6···O2 hydrogen bonds (Table 1) assemble the molecules into interpenetrating sheets which are inclined to (100) by 24.0 and 24.3° and to one another by 25.9° (Figs. 2 and 3).

Related literature top

For background to the properties and applications of imines see: Sun et al. (2001); Boghaei & Mohebi (2002); Liu et al. (2006); Britovsek et al. (2001); Budakoti et al. (2006).

Experimental top

A mixture of 1 mmol (326 mg) of ethyl (2-{(Z)-[(2E)-(2-hydroxybenzylidene)hydrazono]methyl}phenoxy)acetate and 1 mmol (167 mg) of ethyl bromoacetate in 30 ml of ethanol was heated under reflux for 24 h. The resulting solid product was filtered off, dried and recrystallized from dichlomethane solution to furnish pale yellow blocks in 90% yield (m.p. 383 K).

Structure description top

For background to the properties and applications of imines see: Sun et al. (2001); Boghaei & Mohebi (2002); Liu et al. (2006); Britovsek et al. (2001); Budakoti et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Bruker, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2014).

Figures top

	Fig. 1. The title compound showing 50% probability ellipsoids. Primed atoms are related to their unprimed counterparts by the crystallographic center.
	Fig. 2. Packing viewed down the a axis with C—H···O interactions shown by dotted lines.
	Fig. 3. Elevation view of the interpentrating layer packing.

Ethyl 2-[2-((1E)-{(1E)-2-[2-(2-ethoxy-2-oxoethoxy)benzylidene]hydrazin-1-ylidene}methyl)phenoxy]acetate top

Crystal data top

C₂₂H₂₄N₂O₆	F(000) = 872
M_r = 412.43	D_x = 1.280 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 18.2073 (5) Å	Cell parameters from 7734 reflections
b = 11.7758 (3) Å	θ = 4.5–72.3°
c = 9.9950 (3) Å	µ = 0.78 mm⁻¹
β = 93.226 (1)°	T = 150 K
V = 2139.59 (10) Å³	Block, pale yellow
Z = 4	0.16 × 0.15 × 0.07 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2124 independent reflections
Radiation source: INCOATEC IµS micro-focus source	1801 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 4.5°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −13→14
T_min = 0.88, T_max = 0.94	l = −12→12
12339 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0498P)² + 0.7328P] where P = (F_o² + 2F_c²)/3
2124 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₂₄N₂O₆	V = 2139.59 (10) Å³
M_r = 412.43	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 18.2073 (5) Å	µ = 0.78 mm⁻¹
b = 11.7758 (3) Å	T = 150 K
c = 9.9950 (3) Å	0.16 × 0.15 × 0.07 mm
β = 93.226 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2124 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	1801 reflections with I > 2σ(I)
T_min = 0.88, T_max = 0.94	R_int = 0.032
12339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
2124 reflections	Δρ_min = −0.21 e Å⁻³
137 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.65269 (5)	0.39734 (7)	0.64113 (8)	0.0303 (2)
O2	0.60379 (5)	0.59761 (8)	0.72472 (8)	0.0394 (2)
O3	0.57361 (5)	0.65089 (7)	0.51290 (8)	0.0310 (2)
N1	0.74455 (5)	0.21539 (8)	0.94262 (9)	0.0274 (2)
C1	0.66504 (6)	0.28591 (9)	0.60919 (11)	0.0247 (2)
C2	0.69652 (6)	0.21893 (9)	0.71363 (10)	0.0240 (2)
C3	0.70953 (6)	0.10397 (10)	0.68869 (12)	0.0283 (3)
H3	0.7311	0.0577	0.7581	0.034*
C4	0.69152 (7)	0.05673 (10)	0.56450 (12)	0.0314 (3)
H4	0.6996	−0.0218	0.5492	0.038*
C5	0.66146 (7)	0.12522 (11)	0.46220 (12)	0.0308 (3)
H5	0.6497	0.0930	0.3765	0.037*
C6	0.64838 (6)	0.23969 (10)	0.48302 (11)	0.0277 (3)
H6	0.6283	0.2859	0.4121	0.033*
C7	0.71462 (6)	0.27139 (9)	0.84382 (11)	0.0253 (2)
H7	0.7039	0.3496	0.8557	0.030*
C8	0.61552 (7)	0.46587 (10)	0.54257 (11)	0.0284 (3)
H8A	0.5696	0.4282	0.5085	0.034*
H8B	0.6470	0.4784	0.4664	0.034*
C9	0.59814 (6)	0.57753 (10)	0.60731 (11)	0.0274 (3)
C10	0.55682 (7)	0.76451 (11)	0.55916 (13)	0.0378 (3)
H10A	0.6004	0.7979	0.6081	0.045*
H10B	0.5159	0.7618	0.6203	0.045*
C11	0.53530 (8)	0.83464 (12)	0.43762 (16)	0.0463 (4)
H11A	0.5767	0.8387	0.3793	0.069*
H11B	0.5221	0.9114	0.4656	0.069*
H11C	0.4930	0.7995	0.3887	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0445 (5)	0.0230 (4)	0.0226 (4)	0.0049 (3)	−0.0062 (3)	0.0004 (3)
O2	0.0579 (6)	0.0364 (5)	0.0234 (4)	0.0062 (4)	−0.0031 (4)	−0.0042 (4)
O3	0.0402 (5)	0.0251 (4)	0.0273 (4)	0.0064 (3)	−0.0017 (3)	0.0001 (3)
N1	0.0353 (5)	0.0252 (5)	0.0214 (5)	−0.0008 (4)	−0.0014 (4)	0.0006 (4)
C1	0.0270 (5)	0.0233 (6)	0.0241 (5)	−0.0009 (4)	0.0031 (4)	0.0011 (4)
C2	0.0257 (5)	0.0250 (6)	0.0215 (5)	−0.0021 (4)	0.0025 (4)	0.0017 (4)
C3	0.0310 (6)	0.0254 (6)	0.0285 (6)	0.0003 (4)	0.0015 (4)	0.0041 (4)
C4	0.0381 (7)	0.0235 (6)	0.0327 (6)	0.0008 (5)	0.0018 (5)	−0.0033 (5)
C5	0.0359 (6)	0.0323 (6)	0.0242 (6)	0.0000 (5)	0.0010 (5)	−0.0049 (5)
C6	0.0320 (6)	0.0294 (6)	0.0217 (5)	0.0002 (4)	0.0000 (4)	0.0015 (4)
C7	0.0295 (6)	0.0229 (5)	0.0234 (5)	−0.0010 (4)	0.0020 (4)	0.0020 (4)
C8	0.0366 (6)	0.0258 (6)	0.0221 (5)	0.0030 (4)	−0.0036 (4)	0.0017 (4)
C9	0.0293 (6)	0.0280 (6)	0.0245 (5)	0.0003 (4)	−0.0018 (4)	−0.0001 (4)
C10	0.0436 (7)	0.0268 (6)	0.0432 (7)	0.0086 (5)	0.0032 (6)	−0.0040 (5)
C11	0.0472 (8)	0.0350 (7)	0.0578 (9)	0.0141 (6)	0.0135 (7)	0.0127 (7)

Geometric parameters (Å, º) top

O1—C1	1.3720 (14)	C4—H4	0.9500
O1—C8	1.4159 (13)	C5—C6	1.3867 (17)
O2—C9	1.1958 (14)	C5—H5	0.9500
O3—C9	1.3374 (14)	C6—H6	0.9500
O3—C10	1.4537 (14)	C7—H7	0.9500
N1—C7	1.2831 (14)	C8—C9	1.5070 (15)
N1—N1ⁱ	1.4121 (18)	C8—H8A	0.9900
C1—C6	1.3912 (15)	C8—H8B	0.9900
C1—C2	1.4046 (15)	C10—C11	1.5025 (19)
C2—C3	1.3991 (16)	C10—H10A	0.9900
C2—C7	1.4613 (15)	C10—H10B	0.9900
C3—C4	1.3827 (16)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.3901 (17)	C11—H11C	0.9800

C1—O1—C8	117.47 (9)	C2—C7—H7	118.9
C9—O3—C10	115.97 (9)	O1—C8—C9	107.59 (9)
C7—N1—N1ⁱ	111.26 (12)	O1—C8—H8A	110.2
O1—C1—C6	123.70 (10)	C9—C8—H8A	110.2
O1—C1—C2	115.44 (9)	O1—C8—H8B	110.2
C6—C1—C2	120.86 (10)	C9—C8—H8B	110.2
C3—C2—C1	118.49 (10)	H8A—C8—H8B	108.5
C3—C2—C7	122.39 (10)	O2—C9—O3	124.86 (11)
C1—C2—C7	119.11 (10)	O2—C9—C8	125.82 (11)
C4—C3—C2	121.01 (11)	O3—C9—C8	109.30 (9)
C4—C3—H3	119.5	O3—C10—C11	107.37 (11)
C2—C3—H3	119.5	O3—C10—H10A	110.2
C3—C4—C5	119.38 (11)	C11—C10—H10A	110.2
C3—C4—H4	120.3	O3—C10—H10B	110.2
C5—C4—H4	120.3	C11—C10—H10B	110.2
C6—C5—C4	121.16 (11)	H10A—C10—H10B	108.5
C6—C5—H5	119.4	C10—C11—H11A	109.5
C4—C5—H5	119.4	C10—C11—H11B	109.5
C5—C6—C1	119.07 (11)	H11A—C11—H11B	109.5
C5—C6—H6	120.5	C10—C11—H11C	109.5
C1—C6—H6	120.5	H11A—C11—H11C	109.5
N1—C7—C2	122.19 (10)	H11B—C11—H11C	109.5
N1—C7—H7	118.9

C8—O1—C1—C6	5.25 (16)	O1—C1—C6—C5	−178.46 (10)
C8—O1—C1—C2	−174.91 (9)	C2—C1—C6—C5	1.71 (17)
O1—C1—C2—C3	178.99 (9)	N1ⁱ—N1—C7—C2	−179.14 (10)
C6—C1—C2—C3	−1.17 (16)	C3—C2—C7—N1	1.02 (17)
O1—C1—C2—C7	−1.15 (15)	C1—C2—C7—N1	−178.84 (10)
C6—C1—C2—C7	178.69 (10)	C1—O1—C8—C9	171.36 (9)
C1—C2—C3—C4	−0.39 (17)	C10—O3—C9—O2	3.46 (17)
C7—C2—C3—C4	179.75 (10)	C10—O3—C9—C8	−177.91 (10)
C2—C3—C4—C5	1.38 (18)	O1—C8—C9—O2	−11.11 (17)
C3—C4—C5—C6	−0.83 (18)	O1—C8—C9—O3	170.27 (9)
C4—C5—C6—C1	−0.70 (18)	C9—O3—C10—C11	176.28 (10)

Symmetry code: (i) −x+3/2, −y+1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱⁱ	0.95	2.34	3.2802 (14)	168

Symmetry code: (ii) x, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.34	3.2802 (14)	168

Symmetry code: (i) x, −y+1, z−1/2.

Acknowledgements

NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Boghaei, D. M. & Mohebi, S. (2002). Tetrahedron, 58, 5357–5366. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Britovsek, G. J. P., Gibson, V. V., Mastroianni, S., Oakes, D. C. H., Red, S. C., Solan, G. A., White, A. J. P. & Williams, D. J. (2001). Eur. J. Inorg. Chem. 2, 431–437. CSD CrossRef Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Budakoti, A., Abid, M. & Azam, A. (2006). Eur. J. Med. Chem. 41, 63–70. Web of Science CrossRef PubMed CAS Google Scholar
Liu, J., Wu, B., Zhang, B. & Liu, Y. (2006). Turk. J. Chem. 30, 41–48. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

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https://doi.org/10.1107/S2056989014025584

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of ethyl 2-[2-((1E)-{(1E)-2-[2-(2-eth­­oxy-2-oxoeth­­oxy)benzyl­­idene]hydrazin-1-yl­­idene}meth­yl)phen­­oxy]acetate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of ethyl 2-[2-((1E)-{(1E)-2-[2-(2-ethoxy-2-oxoethoxy)benzylidene]hydrazin-1-ylidene}methyl)phenoxy]acetate